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Cheap flights from Chicago Midway Airport to San José from $132

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 2/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:30 am - 11:40 am
MDW
-
SJO
28h 10m1 stop
Multiple Airlines Logo
3:05 pm - 1:56 pm
SJO
-
MDW
22h 51m2 stops
$349Multiple Airlines
Thu, Feb 12 - Wed, Feb 18
Multiple Airlines Logo
1:00 pm - 11:37 am
MDW
-
SJO
22h 37m1 stop
Multiple Airlines Logo
1:30 pm - 7:52 pm
SJO
-
MDW
30h 22m2 stops
$350Multiple Airlines
Sun, Feb 1 - Thu, Feb 5
Multiple Airlines Logo
1:00 pm - 11:37 am
MDW
-
SJO
22h 37m1 stop
Multiple Airlines Logo
12:35 pm - 11:41 pm
SJO
-
MDW
35h 06m2 stops
$354Multiple Airlines
Fri, Feb 6 - Sat, Feb 14
Multiple Airlines Logo
9:22 pm - 11:40 am
MDW
-
SJO
14h 18m1 stop
Multiple Airlines Logo
8:05 pm - 1:56 pm
SJO
-
MDW
41h 51m2 stops
$355Multiple Airlines
Mon, Feb 23 - Tue, Mar 3
Delta Logo
6:00 am - 10:15 pm
MDW
-
SJO
16h 15m1 stop
Delta Logo
7:00 am - 5:45 pm
SJO
-
MDW
10h 45m1 stop
$358Delta
Mon, Feb 9 - Fri, Feb 13
Delta Logo
6:00 am - 10:15 pm
MDW
-
SJO
16h 15m1 stop
Delta Logo
2:25 pm - 10:31 pm
SJO
-
MDW
8h 06m1 stop
$359Delta
Sun, Feb 1 - Thu, Feb 12
Southwest Logo
8:55 am - 7:30 pm
MDW
-
SJO
10h 35m1 stop
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
$360Southwest
Tue, Feb 3 - Tue, Feb 10
Delta Logo
10:46 am - 10:15 pm
MDW
-
SJO
11h 29m1 stop
Delta Logo
2:25 pm - 12:46 pm
SJO
-
MDW
22h 21m2 stops
$363Delta
Mon, Feb 9 - Fri, Feb 13
Delta Logo
6:00 am - 10:15 pm
MDW
-
SJO
16h 15m1 stop
Delta Logo
2:31 pm - 12:46 pm
SJO
-
MDW
22h 15m2 stops
$364Delta
Sun, Feb 1 - Wed, Feb 11
Multiple Airlines Logo
7:30 am - 11:40 am
MDW
-
SJO
28h 10m1 stop
Multiple Airlines Logo
4:15 pm - 2:26 pm
SJO
-
MDW
22h 11m3 stops
$380Multiple Airlines
Sun, Feb 15 - Thu, Feb 19

Frontier flights from Chicago Midway Airport to San José

Our best Frontier deals on Chicago Midway Airport to San José flight tickets
Frontier
Jan 9
MDW6:10 amChicago Midway
7h 26m
1 stop
SJO1:36 pmSan José Juan Santamaria Intl
Jan 12
SJO2:58 pmSan José Juan Santamaria Intl
19h 36m
1 stop
MDW10:34 amChicago Midway
$369
Find similar
Frontier
Jan 5
MDW6:12 amChicago Midway
7h 30m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
Jan 10
SJO1:35 pmSan José Juan Santamaria Intl
8h 52m
1 stop
MDW10:27 pmChicago Midway
$379
Find similar
Frontier
Jan 5
MDW6:12 amChicago Midway
7h 30m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
Jan 7
SJO3:10 pmSan José Juan Santamaria Intl
20h 21m
1 stop
MDW11:31 amChicago Midway
$397
Find similar

Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
Feb 3
MDW8:55 amChicago Midway
10h 35m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
Feb 10
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
$360
Find similar
Southwest
Jan 21
MDW9:55 amChicago Midway
9h 35m
2 stops
SJO7:30 pmSan José Juan Santamaria Intl
Feb 3
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
$405
Find similar
Southwest
Jan 20
MDW5:00 amChicago Midway
7h 50m
1 stop
SJO12:50 pmSan José Juan Santamaria Intl
Jan 31
SJO9:30 amSan José Juan Santamaria Intl
9h 15m
2 stops
MDW6:45 pmChicago Midway
$411
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/12

7:30 am-11:40 am

1 stop28h 10m

San José Juan Santamaria Intl

Wed 2/18

3:05 pm-1:56 pm

2 stops22h 51m

$349

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/1

1:00 pm-11:37 am

1 stop22h 37m

San José Juan Santamaria Intl

Thu 2/5

1:30 pm-7:52 pm

2 stops30h 22m

$350

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 2/6

1:00 pm-11:37 am

1 stop22h 37m

San José Juan Santamaria Intl

Sat 2/14

12:35 pm-11:41 pm

2 stops35h 06m

$354

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/23

9:22 pm-11:40 am

1 stop14h 18m

San José Juan Santamaria Intl

Tue 3/3

8:05 pm-1:56 pm

2 stops41h 51m

$355

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/9

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Fri 2/13

7:00 am-5:45 pm

1 stop10h 45m

$358

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/1

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Thu 2/12

2:25 pm-10:31 pm

1 stop8h 06m

$359

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 2/3

8:55 am-7:30 pm

1 stop10h 35m

San José Juan Santamaria Intl

Tue 2/10

9:40 am-10:55 pm

1 stop13h 15m

$360

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/9

10:46 am-10:15 pm

1 stop11h 29m

San José Juan Santamaria Intl

Fri 2/13

2:25 pm-12:46 pm

2 stops22h 21m

$363

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/1

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Wed 2/11

2:31 pm-12:46 pm

2 stops22h 15m

$364

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/15

7:30 am-11:40 am

1 stop28h 10m

San José Juan Santamaria Intl

Thu 2/19

4:15 pm-2:26 pm

3 stops22h 11m

$380

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $544. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $727. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $506. Flights at noon are often more expensive with an average ticket price of $664.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Fastest flight time

7h 35m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José takes 7h 35m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 7h 35m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Dominical
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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